1. Technical Field of the Invention
This invention relates to the manufacture of 2-substituted-1,3-dioxolanes. More particularly, this invention relates to a method wherein 1,3-dioxolane is reacted with formaldehyde in the presence of an organic peroxide and an ionizable, at least sparingly soluble metal salt initiator under non-acidic conditions to provide 2-hydroxymethyl-1,3-dioxolane and 2-hydroxymethyl-oxymethylene-1,3-dioxolanes. The 2-hydroxymethyl-1,3-dioxolane is useful as a raw material for the manufacture of ethylene glycol. The hydroperoxide is prepared from the 1,3-dioxolane in accordance with a preferred form of the present invention.
2. Prior Art
Kollar U.S. Pat. No. 4,337,371 discloses a method for the preparation of ethylene glycol wherein methanol and formaldehyde are reacted in the presence of an organic peroxide and water to provide ethylene glycol. In a technical article Oyama discloses the free-radical reaction of primary and secondary alcohols such as methanol, 2-propanol, ethanol, 2-butanol and 3-methyl-2-butanol with formaldehyde, and t-butyl peroxide to provide glycols (J. Org. Chem., 30, 2429 (1965). Watanabe et al. in an article in Bull. Chem. Soc. Jpn., 56, 1428-1430 (1983), Vol. 56, No. 5 disclose the reaction of 1,3-dioxolane with electron-deficient alkenes such as diethyl maleate, maleic anhydride, etc. Russian Author's Certificate No. 975,704 (Imashev et al.) discloses a method wherein 1,3-dioxolane is oxidized with molecular oxygen at a temperature of about 10.degree. to 60.degree. C. to provide ethylene glycol monoformate as a principle reaction product.